We-Ko-Pah guys weekend

I’m feeling grateful after a fun guys golf weekend to Scottsdale. We took Friday off and flew down to Arizona on Thursday night for a short 3 day trip. We stayed at We-Ko-Pah Casino and golf resort which is just 25 minutes away from Phoenix airport.

We were able to squeeze 3 rounds of golf in at some great courses. I played okay but unfortunately left a lot of strokes out there. My swing is feeling the best it has in a long time and I feel very close to taking that next step, but it always feels like every round something else comes up. That’s golf of course.

After our early morning tee times, we spent most of the day hanging out at the casino between the restaurants, pool, and blackjack tables. We would finish our tee times around 11:30 and after lunch, we would be showered and ready to hang out by 1. We were all in bed by 9:30 every night so we had some really full and fun days.

It was great getting some good sleep on a guys trip for once. We’re finally growing up and learning.

Unfortunately, we all came out of the casino losers this weekend. I never expect to win when I go to the casino, but it makes the trip a whole lot more fun when you come out a winner. That was the only downside to the trip.

It’s not lost on me that this is likely my last guys trip before my child is born. There will be more trips like this in the future, but they will undoubtedly be different. This trip was especially special for me for that reason.

I’m feeling grateful going into the work week. It’s the last unofficial week of summer. I’m heading to Baltimore to hang out with Sophia’s parents for a few days. Then Sophia and I will spend Sunday and Labor Day back home in San Francisco.

Craziness of life

Prior to this past year, my life has been relatively calm by all standards. I’ve been incredibly fortunate that it hasn’t been crazier.

The last year things started to get crazy with my father in-law having a stroke abroad. We’ve been dealing with my in-laws and their aging and health related issues a lot unfortunately. It hasn’t all been bad though as we’re of course now expecting a newborn in November.

Our calm lives are about to get even crazier with everything going on. I had a glimpse of it last night as Sophia’s flight got canceled. I picked her up from the airport and we went to dinner. After being seated, we were hit with a pregnancy scare which ended up being perfectly at the end. But we had to leave dinner and rush back to San Francisco.

After staying up with Sophia until her early morning flight, I couldn’t get much sleep and woke up feeling just dead. I’ve been running around all morning trying to power through with coffee. I suppose this is good training as to what I can expect when this baby comes.

Life is definitely not going to get easier for us anytime soon. I’m doing my best to embrace it and power through the hecticness. Life is going to get crazy, but it’ll be rewarding.

The decline of department stores

I joke that I was raised in a Nordstrom and Macy’s by my mom when I was young. She would pick me up from school, bribe me with Burger King, and then go shopping. I hated it, but I loved Burger King so I put up with it and would find places to try to nap in the store.

When I went shopping as a kid, my parents would take me to Nordstrom or Macy’s to pick out some new clothes. I still don’t like shopping, but I do always have fond memories of these large department stores holding big events for celebrities or decked out for the holidays. It was part of my childhood.

It was a bit sad to hear that both Nordstrom and Macy’s were closing in San Francisco. I didn’t visit them much as an adult, but I had good memories there growing up and didn’t want to see them gone.

Big department stores have seemed to continue to struggle as shoppers turn online. I suspect most of the new generation that’s hitting the workforce today grew up shopping differently than I did as a kid. It’s a trend that’s been happening and will continue to happen.

I don’t expect many of these big stores to stick around for too much longer. People find it more convenient to shop online with the larger inventories and easy returns nowadays. Along with shopping malls, I’d probably guess that department stores will go largely extinct in the next 10 years.

I’m interested to see what the new trends in shopping will be.

So far, I haven’t seen virtual try-ons take hold yet despite that being a big hype in the startup world a few years ago. I’m wondering if that will eventually become a normal thing soon as technology improves.

I wonder if custom made clothing starts to take a foothold in the market. Imagine a world where you can take a picture of yourself and then have an app build you a custom set of jeans that fit you perfectly in which you can customize.

I can also see a world where department stores like Nordstrom have many more, albeit smaller outposts meant for trying on clothes by appointment and providing that bespoke shopping experience that people still love.

Perhaps I’ll start to like shopping more in the few years ahead.

The last 4 years

I’ve been chatting with a bunch of folks leaving their jobs because they are just simply burnt out from the last few years. It’s been an eventful 4 years for us in the startup world.

We had COVID in 2020 which impacted everyone, but by nature being smaller companies with a burn rate, many startups went through a brutal time. And of course, dealing with COVID was not fun either.

Then we went into 2021 which was a boom year in startup world. The free money effectively made things incredibly good… unfortunately too good. We were having fun. We were growing. But that comes at a cost of working your ass off. I know I was personally exhausted.

Then we went into 2022 when the wheels started coming off the ZIRP train. Startups were bloated and growth came to a screeching halt. The layoffs came hard.

2023 was another tough year with companies adapting to the new reality and VC funding largely dried up. More companies went through layoffs and it was a stressful period for startup builders.

In 2024, things have started to stabilize but it’s been yet another tough year. There’s lots of optimism and glimmers of hope, but most companies are forecasting a much slower growth year.

While these things are cyclical and we can expect more tough years in the future, I’d imagine the last 4 were exceptionally difficult especially those are that are earlier in their careers and have never gone through a downturn like this.

I know I’ve been impacted personally. I feel much more negative at times and I have to catch myself when my mind starts to spiral through negative and worse case scenarios. I often have to remind myself of what I’ve accomplished and learned personally over the years. These tough years will be a blip in the radar in our careers once all said and done.

I’ve done a lot more work on my mental mindset recently. I know that I’m lucky and have things good at the end of the day. I also need to remind myself to celebrate the wins and take breaks to enjoy life.

Today, I did just that. With a stressful morning of 4+ hours of calls, I had a big window in my afternoon and I decided to take a few hours off to relax and enjoy the sunny day here in San Francisco. I’m making up for the lost time now, but those hours in the sun were well worth it.

Epic weekend in Seattle

I took Thursday and Friday off to fly up to Seattle and attend the wedding of one of my good friends from college. It was an awesome weekend filled with exploring, good food, and catching up with old friends.

I spent the afternoons re-exploring parts of Seattle that I haven’t seen in a few years like the U-District and Pike Place. I got some good food at some of my old stomping grounds. One special moment was seeing the owner of Little Thai who has been running the place for 30 years. I first went there about 15 years ago and while I haven’t been back for a few years, she recognized me and we caught up.

The nights were reserved for celebrating my friends. Like always, it was amazing catching up with old friends and seeing what everyone is up to. Now in our mid-30s, we have all gone down different paths in life, but when we get back and see each other again, it’s like we are sitting in our fraternity back in 2009 again.

One thing that is different than in 2009… the recovery time needed after a long weekend like this. With Sophia pregnant, we had early exits both nights and did our best to sleep in as much as possible to get our rest. While I indulged a bit in the drinks, I had kept things under control. We had also flown back Saturday night to recover on Sunday.

Despite all this, I still woke up exhausted this morning. Even with a big rest day on Sunday and a night of good sleep, my body is still telling me that I overdid it this weekend. Getting older can suck in many ways. I’m getting more sleep and drinking less, but it’s apparently not enough still.

Of course there are times where weekends like this are worth it. I have no regret as I was simply celebrating my good friend’s wedding and if the price to pay is a day or two of being tired, then so be it.

But I also see this as yet another sign. My body is calling out to me and telling me that I need even more rest and even less drinks.

Overreactions and overthinking

We kicked off last week with a market stock decline and panic in the air. All of a sudden people had fears of a recession hitting and started selling. A week and a half later, the S&P 500 is up almost 4%.

Don’t get me wrong. There is still a possibility of a recession and more sell-offs in the future. This is the market after all. If there’s one thing I know, stocks will go down again in the future at some point.

However the overreactions to these events usually do not end well. If you had panic-sold last Monday, you would’ve missed the rally back up and left yourself in a bigger hole.

In the private markets, we often see a lot of retail investors overreact and overthink their strategies. People try to predict the future and time the market perfectly on both bullish and bearish sentiments.

The private markets do present more of an opportunity for planning based on external factors so in my opinion, it’s important to pay attention to the trends. But I often see people going all-in when things are going well, or folding completely when things aren’t going well. When you do that, you’re gambling much more than you’re planning.

Belief in equity

Since I started at Secfi in 2018, the overall employee belief in equity may be at an all-time low. If you think about the dynamics of this tough time in tech, you can start to see why.

Employees joined these promising startups in 2019-2021 when companies were growing like crazy and booming. They raised significant capital at high valuations and their equity had been significantly appreciated.

Now with the market correcting itself, their equity has significantly gone down in value. And to make matters worse, many of these companies do not have a liquidity event in near sight. The secondary markets exist for a handful of companies right now, but that’s only for a select few companies out there.

It’s hard to stay the course for many folks given the circumstances. A lot of people have just outright given up on their equity as they may not ever realize value from them, and unfortunately many of them are right.

However, everything is circumstantial depending on the company. And we know that the markets are cyclical. There will be more liquidity events in the future for a lot of companies including IPOs and acquisitions. But to get there, we’re going to need to see things start resetting which hasn’t fully happened yet.

Companies will unfortunately shut down at worst and raise down rounds. Some will emerge from this stronger. However, these things take time and we’ve still yet to see everything unfold.

Preparing for this baby

Last week my friend joked about how I would prepare for the lack of sleep with the baby. He asked if I was going to do some sort of like 2 week sleep period prior to Sophia going into labor. I think he was joking, but it honestly sounded pretty amazing. Although I’m not sure how long my built up energy would last once the sleepless nights come in.

We’re still about 3 months away from the due date, but we’ve started getting all the necessary things for Colin’s arrival like a car seat, crib, etc. Even with only a fraction of the things purchased, the space in our apartment is starting to become more and more cramped.

Everyone says that nothing can prepare you for becoming a parent and that’s kind of how I’m operating. I don’t know if there’s really anything I can do to prepare for the lack of sleep. It sounds like something I’ll just need to suck up and power through when it happens.

I’ve also been doing some reading about kids. I know every kid is different, but I like to be as prepared as possible when he comes. Perhaps that will make me sleep just a bit easier.

Changing up my routine

When I’m working, I’m a creature of habit and like my set routines in order to be as efficient as possible. I go into the office Monday-Thursday and try to be at my desk at 8am. I work out in the afternoons or early evenings and do the same class once or twice a week. Sophia and I cook our workday meals at home, and then finish up work or lounge on the couch watching TV.

Recently, I’ve been feeling that things have been a bit stale. I don’t like doing too much on weekdays to make sure I get enough rest to be efficient at work so my weekdays can seem a bit just boring.

This past week I decided to change things up a bit. Instead of my traditional running class on Wednesdays, I decided to get 9 holes in after work with some friends. On Thursday, we went out to a casual dinner instead of cooking at home. It’s minor changes, but I sit here writing this on Friday and feel a bit more energized heading into the weekend.

It’s a good reminder for myself that I need to go out and enjoy life a bit more and change up my routines from time to time on the weekdays. I hope to try new things in the future like new workout classes or other hobbies.

Prioritizing

I dug my own grave on Monday this week when I said this looks like a light and easy week. It’s the first week of August which is a very popular vacation time and my schedule was wide open. I was hoping to spend the time working through my checklist of to-dos that have been put on hold because of deals.

Of course, it never works out that way. My schedule quickly filled up a ton of unexpected tasks and I am running severely behind on Thursday. After working at a startup for the last 6 years, I should’ve been smarter to know better.

While I perhaps haven’t gotten wiser on that front, I will say that I have definitely gotten a lot better at prioritizing and making sure not to stress too much about everything. Long checklists of to-dos used to give me endless stress, but I’ve learned that is just the norm here when you’re one of the leaders of a startup.

There’s never a shortage of things to do. Ever. Unfortunately, that means that I’m pretty much always perpetually behind where I want to be. That’s part of the life here and I wouldn’t have it any other way.

The Walz VP Pick

The news of yesterday was that Kamala Harris has chosen Jim Walz as her VP candidate. I am a Shapiro fan and thought that would be the best pick, but I’m growing to like Walz a lot. I am far from a political strategist, but it seems that the idea here is to choose someone who can relate to the parts of the country that Kamala does not as well.

Simply put, he’s from the Midwest and speaks like someone from there. He is a veteran who was a former school teacher and football coach. He is wildly different than the prosecutor from the Bay Area, and I’d imagine the hope is that he can help win the Midwest for the Democrats.

So far so good from what I’m seeing from Kamal and Walz. Their rallies and speeches have been electric and they do a good job balancing attacks on Trump/Vance with humor. It’s a night and day difference from the Biden era.

So far we’ve seen Kamala’s team really lean into social media and speak to the younger generation. A month ago, I had thought that the election was all but wrapped up for Trump and the Republicans, but things have gotten a lot more interesting.

It’s still a long ways to go and I want to hear more from Kamal and Walz before I get too excited. But I have hope again which is all we can ask for.

Attacking this day with enthusiasm unknown to mankind

I have a love/hate relationship with Jim Harbaugh. He’s a hell of a football coach that almost led my 49ers to our first Super Bowl since 1994. He had a falling out with the organization and was ousted. He eventually took the job with Michigan and ended up beating my Washington Huskies last year in the national championship.

He’s a bit of an asshole. He rubs people the wrong way. He’s gotten caught cheating and he’s currently under fire for what he did last year with Connor Stallions. All that said, he’s a hell of a football coach and wins.

His sayings and antics corny are as corny as they are effective. I suspect that it works for him because that’s truly who he is. He lives and breathes what he says. He’s not someone to say something and then act differently behind closed doors.

I was listing to Harbaugh on one of my podcasts and one of his famous lines is “attack this day with enthusiasm unknown to mankind”. I didn’t really pay much attention to that in the past or know what it truly meant until listening to him speak about it on this podcast.

In short, he uses this phrase to encourage people to take control of their day. He never liked when people told him “have a great day”, because he wanted to take control and make it a good day. I loved that.

Listening to him speak about this corny saying made me realize that I have fallen a bit into a pattern of lethargy. My weekday pattern recently has been wake up, go to work, workout, go home, cook dinner, watch some TV and go to sleep. I live a good and happy life, but I had not been looking to make my day great.

In other words, I wasn’t attacking everyday with enthusiasm unknown to mankind. Perhaps the opposite actually. Every day on earth is a gift and I don’t know many days I have left. I might as well make every day the best I can when it comes to work, workouts, or fun.

The old internet

At this morning’s team meeting, we had a fun chat about the new generation entering the workforce and also what the old work life was like.

I don’t believe anyone in Gen Z really knows what the classic “I’m on the phone” sign with your hands mean nowadays. They grew up in age of smart phones and I’m not sure if many of them have ever used a typical desktop phone.

Even when I started work 10 years ago, every work station had a phone on the table and we would always call people rather than Slacking them. I think a new hire Gen Z graduate might panic if someone told them to call them via a deskphone nowadays.

I remember back in the day when we had to use dial-up internet and block a phone line to reach the internet. We were never permanently online when we were kids. Now, you can’t be offline.

Downloading a MP3 could take hours and often your download would be interrupted, and you’d have to start the 2 hour process again. I remember having to load my iPod with music and having to delete songs to make room for new music. It’s crazy to think cause now you have the world’s library of music at your fingerprints to instantly play at any moment.

Imagine what life will be like in the next 25 year.

Noise in the markets

It’s generally been a good year for the markets so far. The S&P 500 is up 14.8% YTD. Things have started to stabilize a bit on the inflation front and rate cuts seem to be on the horizon.

As we head into the second half of the year, there seems to be a lot of fear around potential war in the Middle East and the election coming up. As I write this, the S&P 500 is down 1.8% today.

For personal reasons, I don’t pay much attention to the daily changes in the market. I invest for the long-term so the daily fluctuations are simply noise to me.

For work though, we’re also in it for the long-haul and I feel fortunate to not work in a finance job where the daily changes in the market impact my decisions greatly. Of course, we do pay attention to what’s happening in the public markets as it impacts our views in the private markets.

No one likes to see red days like today and no one knows what will happen in these next few months for sure. I do know that there will be a lot more red days and perhaps weeks/months ahead. We knew this could be a tough Q3 and possibly Q4 due to the events in the world.

We’re bracing ourselves, but also hoping for the best. It’s part of the cost of being an investor.

Shitty people

One unfortunate truth that I’ve learned as I get older is that there’s just a ton of shitty people everywhere. It’s obviously a wide spectrum from people who just don’t care about others to being a downright awful person. It’s evident everywhere from work to just walking around day to day.

The internet is full of scammers and people pretending to be who they are not to take advantage of others. There’s that one asshole who opens their car door and drops their litter on the ground. I meet individuals often who will outright lie in order to get paid first.

It can be disheartening at times to see how shitty humans can be. I try to tell myself that everyone’s situation is different and perhaps they were just dealt an awful hand in life which caused them to be this way. Or perhaps they were hurt by others or taught wrongly and if it wasn’t for that, they wouldn’t be that way.

Regardless the reason, I need to do a better job at seeing the good in the world. The reality is that there are more good people than shitty people by a large margin. Unfortunately, the shitty people just tend to stand out more than the rest.

That person that does or says something awful to me can upset me and ruin my day. But the awesome person who helps pick up my headphones after I drop them doesn’t make my day. That’s a bad way to go about life and my own fault.

There’s always going to be people that are shit humans. Karma will take care of them. In the meantime, I need to focus on the good in the world.

Getting older and (possibly) wiser

I am 34 and the last couple years I’ve finally started “feeling old”. Perhaps old is the wrong word and adult maybe the better way to phrase things.

I value my sleep and rest over social life. I feel tired all the time. I no longer get excited for parties, but I do get excited to run errands and go to random stores like Home Depot.

With a baby on the way, I feel very ready to enter the next phase of my life. Of course I’ll miss the 3am nights with friends drinking every now and then, but it’s just not worth it anymore at this age. I look forward to trading in my 3am “nightcap” for a 3am baby feeding session.

Of course there’s a lot of positives to aging. I do feel much wiser. I listen more (but not enough). I know more of how the world works. I don’t let things that don’t matter bother me as much as I used to.

I feel that I’ve become a much better person overall. I’m proud of that part of my life, but I’m equally as proud to that I know that I have a lot of room to grow still.

If I do things right, I know that life should only get better as I age. I look forward to that.

New Mexico

For the second year in a row, Sophia and I went spent the weekend in Santa Fe, New Mexico with her parents during the annual Spanish Market. Her parents have been coming to this event for 30 years and we wanted to be there to help them attend again this year.

This year was much different than last given my father in-law’s stroke. It was tough to see at times. Sophia and I had much more alone time to explore New Mexico last year which we didn’t have this time around as we had to take care of him much of the trip. But despite moving a lot slower nowadays, he still remembers nearly everything about Santa Fe which was remarkable to see.

It was a fun weekend at times, but it was also a difficult one. We knew going in that this wasn’t really a vacation for Sophia or I. This was about spending time with family and ensuring her parents had a good time. It was great to see her parents really enjoying the weekend and have a sense of normalcy after a tough year.

The Democrats and tech

For the last 8+ years, I’ve had many issues with the way with the Democrats have handled most things. The party seems very fractured amongst the far left and the more moderate democrats. The reality is that most of the country is more moderate and the Dems have done an awful job relating to a lot of these folks.

I personally view that social issues outweigh any economic issues in this country so I’m remained steadfast in my commitment to not vote for Trump. But I’ve been more and more disgruntled by the direction of the party.

In regards to tech, it seems that the Dems have just decided to declare war on anyone rich. While there are obviously really shitty rich people out, I don’t subscribe to the thought that any billionaire is a bad person and we need to wage war on them.

This war on billionaires has naturally extended to the war on tech and has caused a rift in the typically very liberal Silicon Valley. This is not a good thing.

Yes, tech has created a lot of wealth, but it has also increased the pie and driven economic growth in the last 10 years. There has been a lot of innovation that has benefited Americans.

Yet, the focus among the Dems isn’t how much tech can improve the country, but rather on the individuals that have generated wealth. Tech has historically been a huge ally to the Democrats and most of their causes.

Until the Democrats can change their strategy here, they will continue to lose support. Given that the future is tech, that’s not a great sign for the party. I hope new leaders can finally figure this out and right the ship.

Wasteful spending

Like a lot of other startups, I feel like we had a ton of wasteful spend back in the early days of the company. When you raise VC money and hire a ton, it was just easy to get lost in software subscriptions, hardware for employees, and stuff for the office.

You start with a cheaper software subscription, add users, and then people forget to monitor that subscription and we run into auto-renewal despite perhaps not using it for the seats we have.

You allow an employee to buy tools to make them more efficient, but then everyone wants that extra monitor, chargers, etc.

We all want swag, but order extra just in case which ends up sitting in a box in the office or in the storage unit.

Unfortunately a lot of the spend didn’t contribute much on the ROI front. I’ve spent some hours this summer donating a lot of these things to high school organizations and Goodwill so that at least someone can use it.

We don’t want to be a company that penny pinches and counts paperclips. But wasteful spending is painful when you start to unravel these things. We’ve done a lot of good work being more diligent about our spend these last couple of years and it’s something I’m proud of.

What is a con-man?

I used to think that conman was just the word for describing a thief. It is widely used today that way. However, the origins of “con” was simply just short for confidence. In other words, it’s someone who has a ton of confidence in what they do.

Someone who wants to make a living as a thief or deceiving someone needs to have confidence to do so. They are just simply incredible at convincing someone else that they are someone they are not.

I am a Democrat born in San Francisco, but I am probably far from the stereotype of one. My views generally align more with the Democratic Party, but I have been just as critical of the far left as I have about the far right. I think the Democratic party needs some serious self-reflection even if they are able to win this election.

However, there’s one thing I know and that’s I believe Trump is a conman who struggles to tell the truth. I think he is in the race solely for his own grab for power, not for the good of the country. For everyone’s sake, I hope I can change my mind on him. But I’ve seen enough over the last 8+ years to form my opinion.

This won’t be a fun 3+ months in America. But I hope that I can write that I’m proud of the way the country reacted. We’ll see.